Addiction grips both main characters. But each sees the blind spots of the other with greater clarity, and these two friends try in their own way to help one another. Jack is terrified of getting married, and asks for Miles' advice. "Do you think I'm making a mistake marrying Christine?" he questions. "Am I doing the right thing? Tell me the truth. I mean, you've been there."
When Miles struggles to stay sober after learning his ex-wife has gotten remarried, Jack tries to encourage him before they spend an evening with Maya and Stephanie: "Try to be your normal, humorous self. The guy you were before the tailspin. Do you remember that guy? People love that guy." Jack tries to blow off a phone message from his wife-to-be, but Miles admonishes him, "You should call her. Call her right now."
Miles eventually lets it slip to Maya that Jack is getting married soon. Furious that Stephanie has been so callously misled, Maya responds with righteous anger and incredulity: "Were you ever going to tell me? Do you have any idea what he's been saying to her?" Indeed, both Maya and Stephanie express justifiable moral outrage at how deeply damaging Jack's lies (and Miles' silence about them) have been.
At a wedding, a priest ceremoniously holds a huge ornamental cross over the couple's head.
Jack's plan for his final week of bachelorhood is to have as much sex as possible. When Miles hints that perhaps this isn't a good goal, Jack reprimands him. "Do not f--- with me Miles," he growls. "I’m going to get laid before Saturday."
Jack's sexual appetite yields a brief "relationship" with Stephanie, and they waste little time before consummating their attraction (offscreen). Later, the camera isn't so bashful, and audiences see Jack and Stephanie going at it in a contorted position. (Jack's backside is exposed in this explicit depiction, as are flashes of Stephanie's body.)
But that's not the worst of it. Rebounding from Stephanie, Jack goes home with a waitress. The next thing we know, he's walking into his and Miles' motel room stark naked. (Audiences get an eyeful of him covering himself with his hands.) It turns out that the woman's husband came home early, forcing Jack to flee the scene sans clothes—and wallet, which contains the rings he's purchased for his impending wedding. Sneaking back into the woman's house to rescue those rings, Miles witnesses the husband administering "punishment" sex to his "naughty" wife. (It may be that the pair planned the adultery and interruption to steal Jack's money.) It's an astonishingly graphic sex scene that features prolonged, full-screen attention to sexual motions, nudity and f-word-filled dialogue. And it's capped off with the naked husband chasing Miles out of the house, fully exposing himself to the camera for several long seconds.
Though Miles' connection with Maya is more substantive than Jack's fling with Stephanie, he too seals the deal, so to speak (behind closed doors). He also buys and pages through a pornographic magazine. (Its cover is seen.) Hardly a scene goes by without Jack making crude comments or obscene sexual references to sex acts and sexual anatomy.
After Stephanie discovers Jack is engaged, she waits for him at the motel and attacks him with her motorcycle helmet. She connects five or six times while hurling obscenities at him and screaming, "I hope you die!" (We see the helmet coming down on Jack, but not the actual impact.) A bloodstained Jack has to go to the hospital, and wears bandages on his broken nose the rest of the movie.
When Miles and Jack are playing golf, an impatient group behind them plays into them. Frustrated, Miles turns around and whacks a ball at them. And Jack runs toward them waving his arms and the biggest club he has.
To explain his facial injuries to his bride-to-be, Jack intentionally drives Miles' beat-up Saab into a tree. When it doesn't do enough damage, he puts a cement block on the accelerator and plunges it into a ditch.
Drug and Alcohol Content
Miles talks endlessly about what goes into making a great wine. The four main characters drink wine in practically every scene (including one in the car, while driving), and they have no problem driving home drunk after each binge.
Miles gets falling-down drunk three times. (The others don't seem to drink less, they just seem to hold their alcohol better.) And he even takes a handful of antidepressants while drinking to try to stave off his paralyzing depression. Desperate for "relief" and near crazy with emotional pain, he begs a server at a wine tasting to give him more than just tastes, then he dumps a spit bucket full of wine on his head. One of the last scenes shows Miles eating a burger at a fast-food restaurant with a bottle of wine surreptitiously hidden beside him.
Maya and Stephanie both smoke.
Other Negative Elements
Miles is shown sitting on the toilet, and is seen showering through translucent plastic.
Miles and Jack stop to see Miles' mom, ostensibly to wish her a happy birthday. But Miles sneaks into her bedroom to steal about a $1,000 from her hidden cash stash. Miles and Jack sneak off before she wakes up the next morning, making it clear that money—not Mom—was the real motivation behind the impromptu visit.
Deception is an obvious thread throughout Sideways. Jack is a systematic deceiver when it comes to sex, saying whatever is necessary to bed women.
A haunting scene near of the end of the film shows Miles in the classroom leading his students through a discussion of John Knowles' novel A Separate Peace. One of his pupils reads a quote from the story's main character: "I could not escape a feeling that this was my own funeral, and you do not cry in that case." The anguish and despair written across the film's two main characters parallels Knowles' words.
At one point Miles says, "My life is over, and I have nothing to show for it. Nothing. I'm a smudge of excrement on a tissue surging out to sea with millions of tons of raw sewage." Raw sewage is not a bad way to describe the unflinching view this film gives us of deeply flawed men. Sideways pulls no punches in depicting how Miles uses wine and Jack uses women to temporarily numb their pain.
Perhaps the movie's one bright spot is Miles' and Jack's genuine care for each other. As twisted as it sounds, Jack's misguided efforts to get Miles hooked up with someone sexually actually reveal how hard he's trying to help Miles snap out of his depression. And Miles is eager to draw Jack deeper into the world of wine (never mind that such pursuits have turned Miles into an alcoholic) to try to give his friend hope and a purpose in life. They want to help, but they're ultimately shown to be too entangled in their own addictions to offer much more than companionship. Neither has what it takes to draw the other out of his destructive world.
Then, inexplicably, Sideways concludes with a trite Hollywood ending that's much more hopeful than anything seen in Miles' and Jack's lives so far. It's an ending that completely fails to hold Jack accountable for his infidelity, or Miles for his embrace of alcoholism. I struggled with it, because I wanted to believe that these men really could get a grip on their addictions and enjoy healthier relationships. But nothing in the film led me to believe that might actually happen.
Thus, the film lapses into the same kind of denial that its characters exhibit throughout. And that submerges whatever merit moviegoers might have glimpsed in Miles' and Jack's friendship in the mountains of raw sewage that has become their lives.